Patent GB-1035092-A (GB)
Title: Improvements relating to herbicides and novel 3-substituted uracils
IPC: C07D239/54
Filed: 1962-12-07
Abstract: Novel compounds of the general formula <FORM:1035092/C2/1> or the corresponding isomeric formula <FORM:1035092/C2/2> wherein R1 represents a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl)alkyl radical containing 5 to 14 carbon atoms or a (substituted cycloalkenyl)alkyl radical containing 5 to 14 carbon atoms; R2 represents a hydrogen, chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxymethylthiomethyl radical; R3 represents a hydrogen, chlorine or bromine atom, an alkyl radical containing 1 to 5 carbon atoms, a chloroalkyl radical containing 1 to 4 carbon atoms, a bromoalkyl radical containing 1 to 4 carbon atoms, or an alkoxy radical containing 1 to 5 carbon atoms; or R2 and R3 together represent a divalent alkylene radical of formula (CH2)n, where n is 3, 4 or 5; with the proviso that if R2 represents hydrogen, R3 represents hydrogen or C1- 5 alkyl; and X represents an oxygen or sulphur atom or a metal salt thereof, are prepared by methods known for the production of uracils, e.g. those disclosed in 968,661.  These compounds are herbicides (see Division A5).  Intermediates. - Ethyl 2 - (3 - cyclopropylmethylureido) - 1 - cycloheptene - 1 - carboxylate is prepared from cyclopropylmethyl urea and ethyl 2 - cycloheptanone - 1 - carboxylate. 6 - Carboxy -3 - (4 - methoxycyclohexylmethyl)-5-methyluracil is prepared from 1-(4-methoxycyclohexylmethyl) urea and diethyl 2-methyloxalacetate. [(3 - Norbornenylmethylureido)-methylene]malononitrile is prepared from norbornenylmethylurea, malononitrile and triethyl orthoformate; with methanolic NaOMe, followed by acetic acid, it gives 3-norbornenylmethyl-5-cyanocytosine.ALSO:Compounds of the general formula:  <FORM:1035092/A5-A6/1> or the corresponding isomeric formula:  <FORM:1035092/A5-A6/2> wherein R1 represents a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl)alkyl radical containing 5 to 14 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a hydrogen, chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxymethylthiomethyl radical; R3 represents a hydrogen, chlorine or bromine atom, an alkyl radical containing 1 to 5 carbon atoms, a chloroalkyl radical containing 1 to 4 carbon atoms a bromoalkyl radical containing 1 to 4 carbon atoms, or an alkoxy radical containing 1 to 5 carbon atoms; or R2 and R3 together represent a divalent alkylene radical of formula (CH2)n, where n is 3, 4 or 5; with the proviso that if R2 represents hydrogen, R3 represent hydrogen or C1-5 alkyl; and X represents an oxyten or sulphur atom or a metal salt thereof, are used to control the growth of weeds, e.g. in a composition containing additionally (i) a diluent which is at least in part an oil (defined as a liquid immiscible with water and soluble in ether, and boiling at not below 125 DEG C), with or without a surface-active agent; (ii) a diluent which is at least in part a solid, with or without a surface-active agent; (iii) a surface-active agent and a diluent which is a liquid other than an oil, e.g. water; or (iv) a surface-active agent.  The compositions may be in the form of solutions, dispersions, powders or dusts, granules or pellets, and may contain adhesives, corrosion inhibitors, antifoam agents, dyes, pigments, anticaking agents, hard water stabilizers and other herbicides, e.g. those of Specifications 1,035,091, 1,035,093, 1,035,094, 1,035,095, 1,035,096, 1,035,097 or 1,035,098, or substituted ureas, substituted triazines, phenols, chloro-carboxylic acids and their derivatives, substituted carbamic acid derivatives, maleic hydrazide, inorganic salts, mixed inorganic-organic salts, or other specified herbicides.